Elizabeth was so frustrated. She was barely sixteen and had never even had a hot kiss. Her hormones were going full blast and she wanted love, romance, and passion like she saw on TV and the web. She was homely and she knew it. Definitely pudgy, with tits that were ample, soft, and a bit floppy, straight brown hair, and glasses. Hell, even her name wasn’t sexy. She went by Liz hoping the glamour of Liz Taylor might somehow rub off but the other kids called her Lizzie. Homely girls need sex too, maybe even more than the pretty ones. Damn, what was a teenage girl to do?
She’d been having a variety of puzzling health problems. Hives and other issues. The doctors ran lots of test and even dosed her with a bunch of expensive meds thinking she might have lupus. She was losing confidence in the medical system.
For at least the past year she had been watching porn, frigging frequently, and finding all sorts of objects as substitutes for penises. She listened enviously to other girls bragging about their busy cunts. Right after her birthday she went to the school clinic and started birth control in a burst of optimism.
Nature had compensated a bit by giving her high intelligence and maturity. Her life changing breakthrough occurred in the AP marketing class which she only took because it fit her schedule. When she heard about product positioning she really paid attention. She needed to find niche or underserved “customers” who would be interested in what she had to offer. Like her, they might not have access to the “beautiful people” of the opposite sex, or maybe limited access to any partners at all. Those limitations could make them very good prospects and appreciative “buyers”. Her customer retention plan was very simple ... make whoever was fucking her feel like the best stud in the world, even if they were only barely started in that direction. Looks were certainly not everything where sex was concerned!
Her first chance to try out this marketing idea happened the next Saturday night. She regularly babysat for a single father who lived nearby. Don was in his early thirties and she stayed with his eight and ten-year-old kids every day after school. His wife had left him for another guy six months earlier. He was a techie and not very outgoing, especially after his marital trauma. They had often visited when he came home from work and Liz could sense his loneliness.
This night he attended a business social function and came home really bummed since he was the only one there without a partner. He had a couple of drinks at the event and another when he got home and now his shell cracked, letting his feelings pour out to the empathetic girl. She moved beside him and hugged him close. This only increased his sobbing. Without thinking she kissed him firmly and their mouths opened into a prolonged passionate kiss. Liz put his hand on her soft breast and his sobs soon turned into moans as they made out. Her vocalizations soon began to match his.
As they undressed each other, Liz softly said, “This is my first time.” He nodded and made love to her gently and thoroughly. She got so high when her first ever oral orgasm hit. It was soon followed by the second one before his erection had even fully filled her eager pussy. This wonderful shaft was about the size of the substitutes she had been using but hotter and with a soft/hard texture they didn’t have. She pushed back with her hips as the heat in her crotch built. Then the third orgasm crested when he spurted the first semen her cunt had ever felt.
Having a real man up close and personal was so MUCH better than she had imagined. Having skin on skin on the outside and the inside of her body was incredibly pleasurable. She wanted so badly to spend the night doing this wonderful stuff over and over but her parents were expecting her. She kissed him goodnight with a new perspective on the world.
They fucked every day when he came home from work. It was the joy of her life. He was an excellent teacher of the love arts and she learned quickly. This was the best phys-ed she ever had. Especially when she was on top where she could exercise most of her body’s muscles, and especially the ones around her vagina. It was so much fun to grip an appreciative hard dick and make it deliver up its love offering. Don even arranged to “be away overnight” from time to time so she could “babysit” when his children were really with their mother. They laughed as she sat on his “baby maker”.
A few weeks into her first affair, her medical symptoms were gone and she was on top of the world. Her body had simply needed the hormones and other special substances that male semen can give to women. At least as important was the psychic balm of being desirable as a female. The doctors were puzzled but she couldn’t explain her “cure” without embarrassment.
Liz’ game plan for a new conquest was this: she would make first contact with her intelligence, get their attention with her mouth, and hook them with her pussy. Since any skills require lots of practice, Robbie, the boy next door, who she had played doctor with years before, got drafted to become part of her sex training program.
All of a sudden he was the recipient of all the oral and genital sex he could get it up for. He was a nerdy horny virgin, smart enough to appreciate this god-send and do his part. First on weekends and then after school. Liz had a key to Don’s house so they would get off the bus there and get naked for an hour of sex experimentation before the children arrived home and she had to care for them.
Internet porn provided plenty of new ideas and Liz discovered things to also try with her older lover. Don always enjoyed the seconds, thirds, or fourths he got when he arrived home, and sometimes left work early to watch the youngsters screwing before fucking her himself. Don was experiencing slippery seconds for the first time since his ex-wife had been fucking around on him, but this time it was hot, not hurtful.
Liz loved bareback, natural sex. Besides the direct sensations of skin on skin, feeling the hot cum rushing out of the dick head to splash deep inside her and then coat their joined parts was very sexy and often gave her at least a small orgasm by itself. Knowing that hundreds of millions of sperm would be swimming around inside her for a long time after the screwing was pretty neat too. It was even more erotic when they were from different cocks!
While Don’s experience was very important for her sex education, she thought that virgins had some real benefits. Like Robbie, they would be more interested in, and appreciative of, her gifts. They wouldn’t need cock wrappers as long as they followed her rules. The physical and emotional joy she observed when they had sex with her the first time was incredibly satisfying, even if they weren’t good at giving her orgasms yet. She felt very special and female. They would never forget her, she knew.
After about three months of a sex life that most teens would only dream about while jacking off, Robbie’s parents got transferred to another state. Liz started a crash course for her young man about identifying, getting, and keeping quality girlfriends. They had a sad goodbye screw. Two months later Liz got an email from him. He had found a girlfriend in his new neighborhood about his own age. She wasn’t a virgin and had pretty good skills in the sack. She was so impressed with Liz’ training that Robbie got hooked up with her older sister who was still a virgin. He was banging them both now and was liking the girl-girl stuff they did too. He sent a picture of himself with two pretty blondes, one shorter and one taller than himself. Liz was very happy for him and they talked on the phone or emailed every month.
With Don’s confidence restored, Liz encouraged him to begin dating. She still babysat when he went out and would be waiting naked in his bed when he returned. When his dates occasionally included sex, he used condoms, and Liz would give him “real pussy” as he told her about the evening. She got turned on thinking about his dick in another, probably prettier, woman earlier, but SHE was the one in his bed now. Even though each would have other partners, they would remain friends-with-benefits and confidants for life. Liz thanked him with her twat, whenever circumstances permitted, for the rest of their lives.
Now that she was truly developing her sexuality, Liz’ confidence and belief in her marketing plan was secure. She selected a classmate who was a homely nerd but always very nice to her and was as bright as she was. Richard also appeared to be physically fit. She asked him about going together to a science expo and he lit up like a street lamp. They had a great time and she observed his eager responses to every attempt she made for physical contact. She held his hand on the drive home and gave him a very hot kiss at her doorstep. His pants bulged nicely, she noticed as they hugged during the kiss.
He had the social smarts to ask her out for a real date and, with her encouragement, got more hot kisses and some tit. He was a farm boy and mentioned a swimming hole at his place.
When she got him to take her there she suggested skinny dipping, which he had only done with his brother and some immature girl cousins. As he saw her get naked, his pecker responded appropriately. Liz noted that it seemed even a bit longer and thicker than Don’s. It looked harder too and she looked forward to checking that out later.
They swam and fooled around in the water, enjoying frequent body contact. After toweling off they sat naked on the beach blanket and ate their lunch. Liz leaned over and kissed Richard, telling him she had brought a very special dessert. He appeared puzzled so she kissed him again with tongue and reached for his perpetual erection. With minimal foreplay she got astride and aimed his pecker head at her gateway to heaven. He filled her nicely and reached for her soft and sensitive tits. A few thrusts later he grunted and blasted a big load of semen against the end of her vagina, his first deposit in a woman. She kept moving on his cock, which never softened, and they climaxed together again after a longer time this round.
They fucked twice more before leaving the pond. Liz was SO hot that night when Don returned from a date and she spread her legs wide for him. He wondered what had gotten into her and, when he found out that it was a new cock, he put his cream in her cunt to join the previous four loads.
Her silly girlfriends talked about fucking like notches on the bedpost. She, on the other hand, was having it as a marvelous emotion-filled experience. Probably getting laid more often and better than most, if not all, the other girls in their high school. Probably even more than her mom!
Having a variety of lovers was great! Don could make love gently and long lasting when circumstances permitted. His recovery time was longer too but he made her feel cherished with his caresses until he could fill her again. The neighbor boy and Richard were quick to get erect even the second and third time. Their vigorous thrusting in her cunt brought quick orgasms for both and the ejaculations were forceful and copious. The differences were exciting. Sex could never get boring.
On the third occasion to be naked with Richard, as they lay together after their first round, he asked Liz, “I know you’ve had sex before but are you doing this with anyone else now?”
One of Liz’ rules was to not volunteer unnecessary information but give truthful answers to questions. She replied. “Yes, why do you ask?”
“I want you to be my girlfriend.”
“Does that mean I would have sex only with you?”
“Yes, I want you all to myself.”
Liz began a conversation that she would have many times in her life. She reinserted him in her cunt and explained her philosophy on intimate relationships. “First of all, Richard, it is my body and I am the only one who decides who I share it with. I am just starting my sex life and you are only my third lover. Already I am enjoying new experiences with you, but if you want to continue enjoying them with me then you must accept me as I am. I really like you or you wouldn’t be inside me right now. I will respect you and answer any questions honestly, and I expect the same in return.”
Richard asked, “Who is your other lover?”
“What makes you think it is only one? I don’t fuck and tell ... another very important thing to remember. You have a lot to learn but I promise you it will be enjoyable if you just go with it. Now, are you ready for some more loving?”
Liz could see that Richard was struggling with the idea of sharing as they got together the next few times but he as he got more comfortable he would make comments like, “Feels really good to me!” and “What have you learned since last time?”
They got together mostly on Saturdays because she was busy at Don’s weekdays and Sunday was family day. The best opportunities for private time were at the farm. They skinny dipped and screwed at the pond when the weather was nice. The barn hayloft was another favorite place.
One afternoon, as they were resting in the hayloft between belly bumping, Richard’s older brother suddenly appeared. “Wow! What have we here?”
Liz scrambled to cover up while Richard simply said, “Hi bro. Would you like to join us? You have to get naked too!” Liz watched wide eyed as a body nearly identical to her boyfriend’s was uncovered. His cock was equally attractive too. They had met, of course, but fully clothed.
Richard turned to the speechless Liz and grinned, “We share a room and skinny dip at the swimming hole so I know he looks like me. Since you like me so much, and you don’t want to be exclusive, I thought you might like a second helping. And he’s a virgin.” Liz was getting hot again and dropped the part of the blanket she was holding. Her pussy was tingling at this unexpected bonus. Both boys’ cocks were ready for action.
Liz said to Richard, “Looks good to me, but I want privacy for his first time. Be back in an hour.” Richard climbed down but stayed within earshot as Liz began the fun process of initiating this young man into the pleasures and mysteries of sex. When he was finally plunging in and out of her snatch she closed her eyes and noted how similar the boys felt. With practice, of course, he would get much better and she shivered with the possibilities.
At the end of the hour his dick was well drained and she sent him to get Richard for his turn. She wasn’t quite ready for group sex but would happily enjoy them one after another. Richard was about to explode as he entered her for the second time that morning. Liz slowed him down, but when she asked, “How does it feel?” Richard said, “Like fucking in silk!”, and blasted his load in with his brother’s cum.
“Go get Robert! His turn again...” Liz ordered.
After three copulations with each boy Liz was tired and getting sore. Her orgasms were triggered as much by her mind as by the two dicks that were stimulating her body. Finally, she begged off until the next weekend. This was an adventure to tell Don about on Monday.
In bed that night she rubbed her clit with the still draining semen from the two boys for one last spasm of delight. Wow, three virgins were now on her scorecard!
On Saturday Liz wanted to go swimming with both boys. They weren’t surprised when she stripped and jumped in. When they swam over to her she grabbed a hard cock in each hand and said, “Happy to see me I notice...” They grabbed her and pushed her underwater where she gave each dick a quick suck before surfacing. After toweling each other off Liz laid back propped up on her elbows. “Who’s first?”
Robert was closer and licked her pussy until it was juicy then slid in. Liz loved to watch a shaft push and pull in her love box as she felt the repeated filling and emptying along with the other sensations from the rubbing flesh. What an erotic sight. It had been a while since they fucked so his dick soon swelled and pulsed to deliver his white deposit. She opened her mouth in invitation to lick the fresh juices from his softening dick while Richard slipped in and repeated the experience. She quivered in orgasm just before he spurted his cream inside her.
Robert was soon ready for more and she got in the scissors position for a leisurely screw with him as Richard snuggled up to her from behind. He reentered her sopping cunt as soon as his brother withdrew.
They swam and screwed the afternoon away, enjoying watching and showing off, which developed into both guys finding ways to simultaneously enjoy the hot girl. She loved all the attention and the pleasure.
That went so well that she invited Richard to accompany her to Don’s house. She introduced Don as her “first lover” and Richard as her “third” and told them she wanted to enjoy them together. Both men eyed each other as they were naked together for the first time.
Liz expected this and said, “You are both good lovers in different ways. Observe carefully and you each might learn something new.” First of all, she made each one watch the other with her then asked them what they noticed.
Of course each man had put on his best show. They spent the better part of two hours competing to give her orgasms and she was happily exhausted when Richard took her home.
The next afternoon Liz’ mother, Marge, came to her room holding several pair of Liz panties. She said they needed to talk and Liz knew what about. “These are obviously cum stains ... I ought to know. This pair even has dried cum still on it. I’ve been seeing these for a while but there are more of them lately. We had a talk about sex a long time ago but you never told me that you had started. As your mother, I need to know what is going on. Don’t worry, I’m not going to get angry or tell your father.”
Liz hesitated, not sure what to say.
Her mother continued, “My mother never talked to me about such an important part of life and I always regretted that. I want us to be closer. My sex life probably started earlier than yours has and I really needed advice because I made some poor decisions.”
That got Liz’ attention since few kids that age think about their parents even having sex. Her eyes opened wide and she blurted out, “Like what?”
Marge had a serious look on her face as she continued, “I will respect your confidence and expect you to keep mine. These are things neither your father nor anyone else knows.” Liz nodded gravely. “A neighbor boy sort of raped me when I was younger than you. I was ignorant, interested in boys, and wanted to be popular. Like you, I wasn’t the prettiest girl around so used what I had. Soon his two buddies were having sex with me too. Fortunately, they knew enough to use condoms during my fertile times. I did enjoy it enough to cooperate but finally realized how much they were using me.
“I didn’t open my legs again until late in high school when I was on birth control. A friend of my father’s taught me what good sex was all about during summer vacation after high school and I had one or two boyfriends all the time through college where I met your father. I was sleeping with other guys until we got engaged and even a little while after. Your dad was taken with me because I was so good in bed but never asked me why. He is the only lover I have had since then. OK, dear daughter, your turn...”
“Wow, Mom! I had no idea! My story is somewhat different because of the talks we had, but it is “like mother, like daughter”. I got on birth control as soon as I turned 16 so I’d be legal and safe. My first time was planned and wonderful. I chose an older experienced man who would appreciate me. Can you guess who it was?”
“Probably Don since there was lots of opportunity.”
“Right! He was a terrific choice and I do him almost every time I babysit. I’ve also done Robbie, the boy who used to live next door.”
Marge interrupted, “And what about Richard?”
“Yup, he is my weekend guy and I’ve started doing his older brother too!”
“Oh my god! You are amazing. Do they know about each other?”
“More or less. It’s a rule of mine that any lover has to accept that I’m not going to be exclusive. I won’t name names though unless we meet as a group.”
“Group too? I never did any guys together though sometimes not far apart. You’ll have to tell me about that some other time ... I’ve had enough to absorb for now. We’ll talk again I hope.”
Don met a woman at a computer club that was a geek like him and he asked her out after interesting conversations during several club meetings. She was about 5 years younger, as tall as he was, quite slender, and never married. She was rather natural and didn’t do anything with her long blond hair except a ponytail.
They went to a computer museum and chatted long into the night after he took her home. She finally asked him if he liked her ... if so why was he still talking? Don got the hint and gave her a kiss which she escalated until clothes came off. He called Liz and said he wouldn’t be home till morning. She was both pleased for him and disappointed for herself, expecting to get laid.
When he dragged in mid-morning she was waiting in a robe and had the kids occupied. He couldn’t get it up and had to eat her to a climax. She was intensely curious so he told her that Rebecca hadn’t been laid for six months and seemed to want to make up for it all at once. He wanted to see, and screw, her again.
Liz said it was a good thing it was Saturday and she had planned to spend the day with her boyfriend. He, and likely his brother too, could make up for Don’s temporary incapacity.
School was out for the summer and Liz wanted to save up money for a car. Don’s kids were going to spend the summer with their mother so that income dried up. She had done office support work for her father and put that on her resume. She watched Craig’s list and, after several dead ends, found an office assistant position with a consultant whose regular person was on maternity leave for the summer. Perfect!
He was about sixty with a lively and witty personality. She took home lots of reading material from his library and impressed him with her quickness. Since they were usually the only ones in the office they soon became close. It was interesting for her to visit new local clients with him, and that direct experience greatly helped as they developed proposals and did reports.
As they got more comfortable with each other, the talk got personal. Her boss, Jerry, had lost his wife to cancer a year earlier. His children didn’t live close so he threw himself into work. His loneliness became apparent to the sensitive young woman as he opened up about his feelings. At the end of the day she gave him a long close hug which became the norm.
Liz soon noticed a swelling in his crotch and realized that sixty-year-old men aren’t “dead”. She began making more physical contact and saw how he enjoyed it. Finally, one Friday when they had just won a big contract, she suggested they go out to celebrate and picked a restaurant which also had dancing. He was surprised but delighted and enjoyed the slow dances especially.
She gave him a special hug and a serious kiss when he dropped her off at home. Her mom was all questions when she came in and wondered what her daughter was up to. Surely she wasn’t trying to seduce such an older man?
That is exactly what the young hottie had decided to do. Using the office legal software, she wrote up a “Release From Sexual Harrassment”, naming her boss, and enclosed it with letter which said, “Dear Jerry: Please accept the gift of my body I am offering you. It is presented with affection and caring and I expect only the same in return. Sincerely, Liz”.
Jerry read the letter and the Release and looked up. Liz was unbuttoning her one-piece summer dress. She had removed her underwear earlier. As her dress fell off she walked to the stunned man and kissed him while moving his hands to her breasts. He held the kiss and began exploring the naked treasure in his arms. Liz pulled back and began removing his clothes, kissing him wherever skin was revealed. She knew he worked out and he was trim and firm. She found some really interesting firmness when his shorts dropped. He was uncut, which was new to her, but plenty big and she took a mouth full. Phil groaned and almost came, but Liz wisely let loose.
She was eager to try out this new love toy so she threw the couch cushions on the floor and spread her legs. She was dripping wet and he slid right in. “Fuck me Jerry, fuck me!”
Years of celibacy spurted from his cock within minutes. Liz held him tightly with her arms and legs as he cried out with joy and then began crying with tears. Liz kissed his wet cheeks and reassured him how much she enjoyed this. She encouraged him to stay inside and he rehardened for a longer time of loving before they parted.
A new bed couch was delivered to the office the next day and it was used frequently. Jerry bought new clothes and worked out even more regularly. Business even improved because of his upbeat feelings.
He was so thrilled with his life that, for her 17th birthday he gave Liz his late wife’s Buick sedan which he hadn’t parted with. It wasn’t “cool”, but the price was right and it had a big back seat, she wryly noted. When she went to pick it up she christened the back seat with her benefactor.
Don, in the meantime, discovered that Rebecca, his new girlfriend, was quite a sexual free spirit. She had lived in a commune during one phase of her life so shared sex was no big deal for her. When Don asked her how many men she had fucked, she smiled and said that would be like her remembering how many meals she had eaten.
She soon learned about Liz’ history with Don and made friends with the young woman. Now that Rebecca was catching up with her needs, she was fine with Liz’ occasional visits and soon joined them in bed. Liz was delighted to learn how two women could have fun together, especially if there was a man involved at the same time.
Among her many talents, Rebecca had worked as a beauty consultant and, even though she didn’t avail herself of much she had learned, she gave Liz some good advice about hair style, makeup and clothing. The rather plain young woman became noticeably more attractive almost overnight. The compliments from her lovers did wonders for her self-esteem. Since her sexual needs were being met, she had stopped the compensatory overeating and was gradually losing the surplus padding, though she hoped her boobs wouldn’t shrink too much.
Of course Don was interested in hearing about Liz’ sex with her older boss. Rebecca reminisced about the older lovers she had bedded.
Don, half teasingly, remarked that if they liked old guys so much maybe they should improve his dad’s sex life. He was 72 and lived alone. His health and mind were good but he didn’t do much socially, which concerned his son. Much to his surprise, the two women decided to do just that. They were both fucking the son so why not do the father too?